My name is Gerry. I moved from New York to California in 2001; I was twenty-one. I had a three-year soccer scholarship to attack. It didn’t quite work out for me, I was plagued with a bunch of niggly injuries, which I couldn’t quite shake physically, so my peers on the course overtook me, and eventually left me for dead. I was still physically fit and exercised every day, I was in pretty good shape.
One of the many courses allied to the scholarship was massage therapy. It was something I never really thought about as a serious career, but figured at least I’ll get to know my muscle groups better, and employ some techniques on myself when I next get injured.
I needed to use warm bodies to practice on, so would offer free sixty-minute massages to some of my friends, and my girlfriend at the time. I became quite good at it and began to understand how to release and relax folk. To be honest with you, sometimes a naked girl in front of you is a bit of a turn-on, but then sometimes it’s not, sometimes it’s the exact opposite. So to be clear, I never used massage as a clumsy way to manipulating a potential sexual encounter. My approach to it was very professional.
One afternoon I got a call from my buddy Josh. Josh worked as the in-house masseuse at the Four Seasons hotel on Hollywood Boulevard. Josh was a keen soccer player, but like me didn’t quite make the cut, so got involved in acting and a little bit of modeling.
Josh had an audition in Venice, so got someone to cover his massage duties at the Four Seasons, however, the cover person bailed, and he rang around his contacts trying to get someone to fill for him, with no success. He finally reached out to me. He was desperate, didn’t want to lose the audition or his job. I was reluctant to help him initially, I had never done this professionally, but I didn’t want to let him down. I agreed. He left all the oils and incense, towels, etc, and talked me through the procedure.
I turned up at the Four Seasons an hour later and gave my first professional massage to a professional Australian surfer called Russell. He had various surfing injuries, and some big muscles needed to be worked on. It was a blessing that it was a sportsman that turned up. I could identify immediately his issues, and get to work on them knowingly. I did a good job, he thanked me, said I had good strong hands, and even threw in an extra twenty bucks on top of the hotel tip.
So that was me. In. Josh started picking up acting jobs, so I started picking up his clients. I got into it. I started reading more books on massage, and even took a couple of courses on the side, expanding and developing my technique. The management at the Four Seasons got to know me too. They began to contact me directly. Within a year, I was working three or four bodies a day, and making some really good money out of it.
A lot of the Four Seasons clientele are actors and actresses coming into town, and working on various jobs. To be honest with you, I wasn’t really into the Hollywood scene, so sometimes I was working on a body, only to be told afterward, they were moderately famous, or the next big thing.
Remember I mentioned before about my approach to massage being wholly a professional pursuit? Well, that was about to change.
One afternoon a very famous actress lay on my massage table. I recognized her immediately. She was in a film I had watched repeatedly, she was in town I guess working on a film. I am busting to tell you who this actress was, but I would never betray a confidence. For the purposes of this story, I am going to call her Gemma. She must have been around forty years old, with long dark hair. Physically fit, not a generic skinny actress, well-toned, and strong muscles. Yoga fit for sure.
There wasn’t much chit-chat between us. She had some tightness on her hamstrings, particularly her right leg. I soon got to work on them. She kept on a t-shirt and underwear. Her underwear was nothing special, black, perfunctory, no-frills. Some folk take off everything and are discretely covered by towels as I go to work. I prefer if females keep on their underwear then there is no confusion or temptation.
I worked solely on her legs, with maybe ten minutes in the end on her upper back and neck, just to finish off the session. Her legs were long, tanned, and elegant, I enjoyed touching them, and getting into her muscles. She seemed happy, thanked me and signed her hotel bill, and probably threw in a gratuity I can’t remember. Before she left the room, Gemma asked me if I would be available for more sessions over the next couple of weeks, but that it may be difficult to organize as her schedule was kind of erratic. How late do I work, etc? I said I would do my best to be available, but best go through the hotel’s booking service and ask for Gerry.
A few days go by and I get a call from my boss at around 8.30 pm, asking if I can do a 9 pm. I was about to say, sorry I am too busy, but before I could he mentioned it was from Gemma, she had just finished on set was traveling back to the hotel, and needed some work done. Of course, I agreed immediately. My girlfriend was pissed off, but I assured her this client would pay double for the inconvenience.
It was around 9.45 pm before she finally showed in my room. She apologized for being late, she had stopped by her room for a quick shower and wandered over to my massage room in a hotel robe and slippers, which clientele often did. She asked me to continue work on her hamstrings. She took off her robe and lay on my table. She was wearing a loose-fitting white vest, with no bra. I could clearly see the shape of her breasts, areola, and nipples. Probably a C cup. Yellow underwear, somewhere between panties and a G-string, but again, looked like something clean just grabbed from a drawer, after she had her shower.
I attached the headrest and asked her to lie on her front initially. I began getting to work on those hamstrings. After a few minutes, she asked if I wouldn’t mind applying less pressure. Whenever I hear that, it usually means the client is tired and is using the massage to get rid of the day’s stress and pressure. So I obliged. I mixed up my oils and my massage strokes were more soothing, sensual. I offered to work on her back, which she said sure, she took off her vest and lay back down.
I began to apply some sensual strokes to her back. The side boob on display was quite erotic. I was applying long languid strokes all over her back and neck, to the top of her ass. I didn’t quite realize this was happening, but it suddenly dawned on me that my dick was semi-hard. I won’t lie, I was enjoying massaging this forty-something woman. There was something in the way her body relaxed and responded to my hands. I was hitting her trigger points, and she was winding down. I liked the smell of her skin too. Sure there was probably a heady mix, of the shower gel and the oil I was using. Whatever it was, I was most definitely getting somewhat aroused.
Gemma began to drift off, and before long she was asleep. She had repositioned her head and lay on her left cheek. I could see her right cheek and mouth, covered with her messy long shower wet hair. She looked quite beautiful in repose.
That night when I drove home I couldn’t stop thinking about her. My dick was hard. It wasn’t because she was a famous actress, that wasn’t the turn-on. It was about the massages and the connection between us. I had never quite felt the way I felt, even when I massaged my girlfriend. Maybe it’s because she was older and more relaxed, I couldn’t quite work it out.
I spent the next week thinking about her every day. I lost a little focus on the tired old bodies I was massaging now daily, they weren’t getting the best version of me that’s for sure. Who knows where Gemma was, maybe she was on location further afield and returning in the early hours, who knows? I knew she was still in the hotel though, I’d surreptitiously found that out from one of the waiting staff who worked there.
Again I get a call from someone at the Four Seasons, asking if I was available for a late massage. Again my girlfriend was unimpressed. I couldn’t get in my car quick enough and drove to Four Seasons. I felt euphoric, and you guessed it, my dick was getting hard again.
This time Gemma turned up around 10.15 pm and was profusely apologetic, thanks for waiting, and sorry that she was inconveniencing me. I made her feel at ease, saying, don’t worry I was used to working at unusual hours, which was a lie, I was only doing this for her. She has freshly showered again, in her hotel robe and slippers. I asked her if there were any specific areas she wanted me to work on. She said she felt a little tight around the hips, and if we do some work there, but mainly, she just wanted something to ease her towards her having a good night’s sleep, like the last time.
She took off her bathrobe and was wearing the same white vest. The shape of her breasts moving under the vest gave me an instant hard-on. It wasn’t just her breasts, it was her neck and face, and towel-dried her. Her smell. This was slowly becoming a problem for me to maintain a professional distance. Her underwear was white too, the flowered pattern on the front, a slight teasing window to her bush. Again though, probably worn a hundred times, and had seen better days.
I asked her to lie on her front again, and we would do some back and legs. I held up a towel and allowed her to take off her vest. I spent the next forty-five minutes or so working her back and legs, and like before she drifted off. There was some sensual music playing and it seemed to do the trick. I was semi-hard the whole session. I was beginning to move my hands towards more intimate areas. Digging into her glutes a little, brushing the side of her breasts. I was so turned on.
Gemma revived a little and asked if I would mind stretching out her hips as we had discussed. She turned over and put her vest back on. She asked if I would dim the lights, which I did, but also offered her a face visor, which she took and put on.
I stood at the side of my table, and lifted her left leg, and began to stretch it in circles. She was so tired from the day, I could take the whole weight of the leg. I rotated her left leg gently in circles, opening up her hip sockets. Holding it and moving it in a counter-clockwise direction. This is where my arousal or manipulation began to take charge.
As I stretched out her leg, her loose-fitting underwear would free up a little. I moved her leg in such a way that the material on her underwear slowly revealed the left side of her pussy. My cock was hardening. I persisted in moving the leg, willing the material to free up some more. It did. After a couple of minutes of this, I had now a full view of the left side of her pussy. It was a little bushy, but her lips were a little swollen. Prominent. I hadn’t seen a pussy like this before, maybe it’s because Gemma was older. I looked at Gemma’s face, her mouth, her lips. Fucking hell. Sexy as fuck. I angled my head a little and tried to get an even better sight of her pussy. The lights were dim, and it wasn’t quite happening.
Gemma was emitting a gentle snore. So even if I was in full pervert mode, at least the job was being done. I lay down her left leg and moved around the table to begin working on her right leg. I applied the same technique, and again my very clear goal was to somehow dislodge the material of her underwear to reveal her pussy to me. The narrow strip of material covering her pussy had folded in on itself, so I was getting a much clearer view. The right side of her pussy came into view. A beautiful swollen lip. I wanted to touch it, I wanted to kiss it, I wanted to taste it. My cock was fucking solid.
I had been obsessing about seeing her pussy, that I completely disconnected from her top half. What had happened by sheer chance was that her right breast came free from beneath the loose-fitting vest. Her whole breast was exposed. Her areola was dark, and maybe an inch in diameter. Her nipple was pointed. I noticed she had a little scar, on the south side of her areola. Maybe a surgery? It didn’t look like any kind of boob enhancement. What do I know? It looked sumptuous, all I could think of was putting my whole mouth over it. Just as I was thinking that, Gemma flipped her visor a little, she was coming round. She adjusted her vest and covered up her breast without a fuss. We finished up, she put her robe back again, and then before she left, she actually gave me a quick hug. Thanked me repeatedly. Went back to her room.
The Four Seasons has an underground parking area, it’s dark. Before I drove home for the night. I found an old t-shirt, which I had used at the gym earlier. Placed it to the side. Pulled down my shorts, took out my fully swollen cock, and masturbated. Little images of Gemma’s breast, nipple, pussy filled my imagination. It didn’t take long before my cum spattered into the t-shirt. I can honestly say it was the best most fulfilling wank I have ever had.
Over the next few days, I spunked into another t-shirt, or training sock, or whatever the fuck was lying around. I think one day, I tugged away at least four times. Needless to say, as a professional masseuse this was becoming a problem. I couldn’t get Gemma out of my mind.
A few days passed, it was a Sunday afternoon. I had to do some massage work on a visiting junior swimmer, who was in town for a competition. He had some shoulder issues, which I did my best to iron out. It was around 3 pm and that was me done for the day.
Just as I was heading out, I bumped into Gemma in the lobby. She had running pants on, a sports bra, cap. She looked fit. She was sweaty. So fucking sexy.
She said it was a shame I was leaving for the day, and could I recommend anyone else, as she is still feeling a little tight in the hips, and needed some manipulation. Yes right, I was going to offer up this amazing body to someone else. I said, don’t worry, I’d make a call, and see if I could shift something around. This was a complete lie, but I didn’t want to seem too eager or reveal my obsession with her. We traveled back up the elevator together and headed to my massage room. Feeling like she was impinging on my time, she asked it was okay to not take a shower, and just get to work on the hips. I said fine, which was probably a good idea, as her muscles would still be warm from her jog.
I set up the massage table, put on some music, dimmed the lights. I gave her a towel to dry down her sweat. She asked if she should take off her running pants, what would be best? I said probably, and we could really get into some proper hip rotations. She took off her running pants, she was wearing a cheeky G string. This was fucking torture for me, my cock began to swell. The G didn’t cover much at all, it was just about see-through, her bush was clearly visible. She lay on the table and asked if it was okay to take her sports bra off. Of course whatever she wanted. I held up a towel, and she threw her sweaty top in the corner of the room. She lay on the table with a towel covering her breasts.
I was a lot more vigorous with Gemma’s hip treatment. The muscles were warm, she wasn’t tired, and I could be a little more aggressive. She was also awake and was, for the first time, a little more chatty. I basically didn’t know anything about this woman, she was intensely private. Of course, being more vigorous with the hip rotations was perfect for me. It allowed me greater access to, let’s not pretend, feast my eyes on her pussy. I began rotating her hips, which she was enjoying, we locked eyes quite a few times during this. Occasionally, she would close her eyes, which was my opportunity. I glanced down, and the material from her G hadn’t fallen aside like the last material, but had ridden up and was resting against her clit, both pussy lips enveloping the G material. What a sight. I couldn’t keep my eyes away. My cock was bursting to get out of my shorts.
We continued the session. I am not sure if Gemma was aware of what she was displaying to me, but the probability is, that this smart beautiful lady knew exactly what she was showing to me, and was so comfortable, that she didn’t really care. In thirty minutes, she’d be out of here, and whatever, a young masseuse had a flash of her cunt. Big deal.
The last twenty minutes of the session saw a strange turn in the mood. Gemma was face down now and I was massaging her back. Going deep. Of course, the spectacle of the reverse G is also quite pleasant. The string running down her ass crack would have revealed another splendid view of her pussy. I maintained a modicum of respectability though and covered her lower half with a towel as I got to work on her back.
Gemma slowly drip-fed some information about herself, as I probed deeply into her back. She was here by herself, feeling lonely, vulnerable, not particularly cherished in her current employment. I refuse to offer any advice to clients, I am not a shrink, but I know that I can help them shake loose the tension that they are feeling. I could feel it coming, but then it happened Gemma began to cry, big teardrops falling onto my table. I offered her comfort. The gentle massage continued. I finished the session working on her scalp and temples. Encouraging release and relaxation.
The Four Seasons has plenty of bathrobes, so I fetched her one, which she put on. She picked up her sweaty clothes and thanked me. Before she left she gave me a tight hug.
Guess what? My cock was rock solid. Most likely pushing against her, and almost certainly, she would have been able to feel it against her body.
I sat there for a few moments, not knowing what to do, something was stirring in me. I contemplated jacking off over the massage table. I took a breath to calm down. Then I noticed Gemma had left her cap.
I locked up for the day and was intent on leaving the cap with the reception, but I knew where her room was. I rerouted my elevator journey and found myself outside Gemma’s room.
I knocked gently, and she answered after a few seconds. She still seemed a little worn out, post crying, and ushered me inside for a minute. I returned her cap and made sure she was okay. She again thanked me profusely. I could hear a shower running in the other room. She was still in the robe, I gave to her. She looked at me and came close to me, almost like she would kiss me. I was nervous. She again hugged me this time for a long moment. She then rested her head against my chest, I was probably a foot taller than her. I wasn’t quite sure where this was going, if anywhere. She sort of swiveled in the embrace, where I was now enfolding her. Her back was against my chest, and she grabbed my arms and made sure I was clenching her tightly.
I was so glad to do this, it was a long moment. She then arched her head towards me, whilst staying in this tight clench. She looked at my mouth put her left hand on my mouth, leaned in, and kissed me, I kissed back. Then she came out of the kiss, and back in the clench her back still resting on my chest.
I kissed her neck. I could hear breathing becoming a little more rapid, maybe her heart pumping a little faster. My cock was fucking solid.
Her robe tie had come a little loose, I looked over her shoulder, and down inside her robe. Her left breast was in clear view, her nipple had popped up, and was hard.
Either I grabbed the robe at the collar and began to lever it off, or she dropped her shoulder allowing it to fall, or perhaps a bit of both. The robe dropped to the floor. Her naked back was against my chest. Her breathing was becoming a little more excited. Gemma stayed in the same position, but I moved round in front of her. She was a little shaky, vulnerable perhaps. Shy? I kissed her again. This time we were open-mouth kissing.
She had moved back a little to steady herself and was now resting on a wall. I pulled back a little and just drank in the sight of her two beautiful tits. I had dreamed of this. I moved down and began sucking on her right breast, biting, nibbling, tonguing her nipple. My cock at this point was on fire, the blood rushing to it was incredible. It actually felt a little painful. As I continued to suck on Gemma’s tit, she put her left hand on her left breast, and slowly moved my head onto that. I began licking and sucking her left tit. Biting into it. I kept my left hand on her right tit, tweaking her nipple. Both her nipples were red and raw.
I began moving away from her breasts down her body. It was still sweaty with her exercise and the oil from the massage, her smell was turning me on. She still had the G-string on from before. I pushed my nose into her, onto the cloth of her G-string. There was a feeling inside me just to take it off and go to work on this beautiful pussy, but I held back. The tease that had me jerking off for the last couple of weeks, I wanted to take further. I peeled back the G, revealing what I had seen on the table, the left side of her pussy. I kissed then licked the length of her left outer labia. I took my thumb and folded open her pussy lips, moving closer inside. I took the tip of my tongue and began exploring the softer more delicate inner labia. I was tasting her. Pools of pussy juice were beginning to form in the inner labia. I was moving my tongue towards her vaginal opening. I had a quick glance up to see if Gemma was enjoying this.
The sight of her breast-hardened nipples was joyous. Gemma was looking right down at me, into my eyes, watching me indulge. I scooped some pussy juice from her slowly gaping hole, with my fingers. I reached up and coated her right nipple. I ran my fingers over her little areola scar. Meanwhile, my tongue continued to probe her beautiful cunt. I wanted to explore her hole but had some business to do with her right outer labia. I reached around her left buttock cheek and began to lever off the G-String. Gemma let out a little moan, as her G-string was removed.
I began to kiss, and nibble her right outer labia. With my thumb, I cleared away some of her pubic hair. I folded back her outer labia, and begin to tongue the flesh of her inner labia.
Gemma had rested her hand on my head, stroking my hair. I was now using both my hands and fingers to delicately move in and explore every part of her gaping hole. I used the surface of my tongue, and licked from her perineum, up along the whole length of her pussy, and finished on her clitoral hood. I began to slowly manipulate her clit with fingers and tongue. The blood gushing to my cockhead felt like it would explode. I wanted so much for my cock, to be deep inside this delicious cunt, but I wanted to play some more. Gemma’s vaginal hole was dripping now. I placed my whole mouth over her pussy and began to really eat her out. Like I was munching on a peach or mango. The juices were covering my mouth and chin. The taste of sweat, massage oil, and cunt juice created an insane cocktail.
I sneaked a peek up at Gemma, who was in the zone. Her body was beginning to shudder, her pussy was responding to my mouth and she was offering more to me, drawing my tongue into her hole. Gemma lifted her left leg and placed her foot gently on my right shoulder. Her whole pussy opened up, it was a wonderful sight. I couldn’t stop eating it. I was devouring it.
“Oh fuck, I’m cumming,” she whispered. “You’re making me cum!” I had never made a woman cum, with oral stimulation, so this was a bit of a first for me.
Her body writhed, even more, she grabbed a handful of my hair and pulled me in. “Oh fuck, I’m cumming, I’m fucking cumming!” An orgasm writhed through her whole body.
Gemma reached over and began to take my T-Shirt off. The motion pulled my mouth off of her cunt. I stood up, and we began kissing each other, I could tell she was tasting her own cunt from my chin.
Gemma then began to explore my chest. I didn’t exactly have a six-pack but had a strong physique, she rubbed her hands over my midriff, feeling my abs. It couldn’t have escaped her notice that there was a raging hardon busting to get out of my shorts. “Can I take these off?” So polite. Now it was her time to have some fun. She spun me around a little and started peeling my shorts over my buttocks, then they fell to the floor. Gemma ran her hands over my buttocks for a second. It was my cock she wanted though.
I had a look down at my cock, it was the biggest and the thickest I had ever seen it. All I wanted to do now, was put it deep inside Gemma’s beautiful cunt. I felt this is what Gemma wanted too. She began to turn me around, she was getting set for me to fuck her. When she saw how hard my cock looked though, she changed plans. I genuinely think, that no one had ever worked her pussy the way I just did. She decided to give me something back.
She got down on her knees and took me all the way in her mouth. It was a sensational feeling. She wasn’t agitating it, in a bid to make me cum. She was playing with it, caressing it, tenderly and with love. It wasn’t about seeing how much she take down her throat. There was a quietness to it. Her hands were reaching around my arse. Her hands covered my buttocks, with her fingers tips, working down my arse crack. She pulled me in a little, and I looked down watching my cock go a little further into her mouth. I wanted to see her face, I moved her hair from her face, and stroked her cheek with the back of my hand. I could see the shape of my bulging cockhead pushing against her inner cheek. She didn’t once glance up to see if I was enjoying this, she just knew I was. Her focus was on my cock, and how many different ways she could suck it.
I was so close to blowing my load. I had a minor conflict that this may be rude, she may not like swallowing on the first date.
“Can you put this inside me now, baby?” Jesus! That in itself could have made me blow my load, but I willed it not to.
Gemma stood up, she kissed my mouth then turned round, she pushed her hands onto the wall. Pushed her arse out towards me. I looked down. This is a picture I will die with. It’s etched on my brain. I have thought about it a lot over the years, it’s my go-to memory if I want to jack off. Here and now though, the sight of Gemma’s cunt was glorious, it was swollen, wet, and opened like a beautiful flower.
I took my cock and guided it towards her hole, maybe on another day I may have put the cock head on her clit, and teased her a little, but it was too late for that, I just wanted to be inside this woman. I placed my hand on her lower back and guided my thick swollen cock deep inside her.
“Oh fuck, oh fuck, that feels so fucking good,” she trembled. I didn’t even want to thrust, I just wanted to rest, with my cock beautifully snug in her cunt. Gemma had other ideas though, she began to move, and motion her cunt around my cock. I began to slowly thrust, back and forward working beautifully with Gemma’s pussy muscles clamping my whole cock, then releasing it. I didn’t want this to end. We found a nice rhythm, I think we both sensed this wasn’t necessarily about pushing for an orgasm, but more about finding the joy in fucking each other. That said I was so close to blowing the lot. Gemma sensed that. She looked over her shoulder and pulled me towards her, we kissed some more. I was more upright now and began thrusting my cock up inside her. My hands were now clamped on her breasts. “You’re fucking me, you’re really fucking me!” It was a turn-on hearing this and pushed me closer to blowing my load.
Gemma suddenly levered herself off my cock. Hurriedly grabbed my hand, and pulled me around the corner to her bed. She pushed me onto the bed. The cover felt nice on my skin. I glanced down, and my cock was still solid. Gemma ran her hands down my legs. She had a clear intention of getting on top of me, and riding me, but I didn’t expect her to do it in this fashion. She stood up on the bed, her feet astride me. Crouched down, still on her feet, and lowered her delicious cunt onto my cock. Slowly and teasingly, we both watched as my cock disappeared inside her cunt. She had her left hand placed behind for balance. I did say she was Yoga-fit. She was in control, I was passive. Her eyes were closed, enjoying the sensation of sliding up and down my cock. The pace began to increase, I noticed she has was biting her lip a little, her mouth looked sweet. I placed my thumb, on her lips, and she started sucking my thumb.
Her face began to crease a little, I could sense she was about to orgasm. Both of her hands were propping her up, as her sopping cunt continued to pump on my cock.
Her whole body was open for me, her breast looked soft and creamy, with nipples enlarged. “Oh, fuck I’m cumming, I’m cumming baby!”
I couldn’t remain passive, I sat up. Put my hands on her ass cheeks, and began to work my cock deeper inside her. This propelled her to the next level, she began more vocal. “You’re fucking me, you’re really fucking me!” She was now sitting on me with her arms around me, we clenched each other tightly. “You going to cum for me, baby?” This was all the encouragement I needed, my balls emptied a long jet of hot spunk inside her pussy, it felt glorious, but I wasn’t finished. I dug my fingers into her ass cheeks and pulled her down. Her pussy reacted and tightened on my cock, as a second stream of semen filled her pussy. “I’m still cumming!” As was I. We both exhausted our fluids, as she softened and crumpled on top of me. I was still inside her. My cock eventually softened, Gemma sat up and let my cock slide out of her pussy. Our intertwined fluids slid out of her cunt, and formed a pool on my abdomen. We lay side by side on her soft creamy sheets, and from memory, we both nodded off, I think.
This event happened just shy of twenty years ago. It is still vivid in my imagination. It is still the most singularly spectacular sexual experience of my life. I’m forty-two now. Gemma still works in TV and movies. I’ve seen her pop up in a few things, she must be around sixty now, and she still looks fucking hot.
Gemma did visit me for one final massage by the way, but I’ll save that story for another time.